Cefonicid

{{Short description|Chemical compound}}

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{{Drugbox

| Watchedfields = changed

| verifiedrevid = 443509375

| IUPAC_name = (6R,7R)-7-[(2R)-2-hydroxy-2-phenylacetyl)amino]-8-oxo-
3-{[1-(sulfomethyl)tetrazol-5-yl]sulfanylmethyl}-
5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

| image = cefonicid.png

| tradename =

| Drugs.com = {{drugs.com|CONS|cefonicid}}

| MedlinePlus = a601206

| pregnancy_AU =

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| routes_of_administration =

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| protein_bound =

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| CAS_number = 61270-58-4

| ATC_prefix = J01

| ATC_suffix = DC06

| PubChem = 43594

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| DrugBank =

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 39734

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 6532B86WFG

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG = D07644

| ChEBI_Ref = {{ebicite|correct|EBI}}

| ChEBI = 3491

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 1601

| C=18 | H=18 | N=6 | O=8 | S=3

| smiles = O=C2N1/C(=C(\CS[C@@H]1[C@@H]2NC(=O)[C@H](O)c3ccccc3)CSc4nnnn4CS(=O)(=O)O)C(=O)O

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 1S/C18H18N6O8S3/c25-13(9-4-2-1-3-5-9)14(26)19-11-15(27)24-12(17(28)29)10(6-33-16(11)24)7-34-18-20-21-22-23(18)8-35(30,31)32/h1-5,11,13,16,25H,6-8H2,(H,19,26)(H,28,29)(H,30,31,32)/t11-,13-,16-/m1/s1

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = DYAIAHUQIPBDIP-AXAPSJFSSA-N

}}

Cefonicide (or cefonicid) is a cephalosporin antibiotic.{{cite journal | vauthors = Saltiel E, Brogden RN | title = Cefonicid. A review of its antibacterial activity, pharmacological properties and therapeutic use | journal = Drugs | volume = 32 | issue = 3 | pages = 222–59 | date = September 1986 | pmid = 3530703 | doi = 10.2165/00003495-198632030-00002 | s2cid = 243051006 }}

It has a density of 1.92g/cm3.

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Synthesis

Injectable semi-synthetic cephalosporin antibiotic related to cefamandole, q.v.

File:Cefonicid synthesis.svg|inventor1-last=Berges|inventor1-first=David Alan}}D. A. Berges, {{US patent|4048311}} (1977 to Smith Kline).{{US patent|4093723}}, {{US patent|4159373}} (1978, 1979 both to Smith Kline).]]

Cefonicid is synthesized conveniently by nucleophilic displacement of the 3-acetoxy moiety of 1 with the appropriately substituted tetrazole thiole 2. The mandelic acid amide C-7 side chain is reminiscent of cefamandole.

See also

References